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Ring-Expansion Reaction of Oximes with Aluminum Reductants
The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl(2), AlH(3) (alane), LiAlH(4), LiAlH(O(t)Bu)(3), and (MeOCH(2)CH(2)O)(2)AlH(2)Na (Red-Al) were examined. Among reductants, AlHCl(2) (LiAlH(4):AlCl(3) = 1:3) in cyclopentyl methyl eth...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2012
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268446/ https://www.ncbi.nlm.nih.gov/pubmed/22699568 http://dx.doi.org/10.3390/molecules17067348 |
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author | Cho, Hidetsura Iwama, Yusuke Mitsuhashi, Nakako Sugimoto, Kenji Okano, Kentaro Tokuyama, Hidetoshi |
author_facet | Cho, Hidetsura Iwama, Yusuke Mitsuhashi, Nakako Sugimoto, Kenji Okano, Kentaro Tokuyama, Hidetoshi |
author_sort | Cho, Hidetsura |
collection | PubMed |
description | The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl(2), AlH(3) (alane), LiAlH(4), LiAlH(O(t)Bu)(3), and (MeOCH(2)CH(2)O)(2)AlH(2)Na (Red-Al) were examined. Among reductants, AlHCl(2) (LiAlH(4):AlCl(3) = 1:3) in cyclopentyl methyl ether (CPME) has been found to be a suitable reagent for the reaction, and the rearranged cyclic secondary amines were obtained in good to excellent yields. |
format | Online Article Text |
id | pubmed-6268446 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62684462018-12-12 Ring-Expansion Reaction of Oximes with Aluminum Reductants Cho, Hidetsura Iwama, Yusuke Mitsuhashi, Nakako Sugimoto, Kenji Okano, Kentaro Tokuyama, Hidetoshi Molecules Article The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl(2), AlH(3) (alane), LiAlH(4), LiAlH(O(t)Bu)(3), and (MeOCH(2)CH(2)O)(2)AlH(2)Na (Red-Al) were examined. Among reductants, AlHCl(2) (LiAlH(4):AlCl(3) = 1:3) in cyclopentyl methyl ether (CPME) has been found to be a suitable reagent for the reaction, and the rearranged cyclic secondary amines were obtained in good to excellent yields. MDPI 2012-06-14 /pmc/articles/PMC6268446/ /pubmed/22699568 http://dx.doi.org/10.3390/molecules17067348 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). |
spellingShingle | Article Cho, Hidetsura Iwama, Yusuke Mitsuhashi, Nakako Sugimoto, Kenji Okano, Kentaro Tokuyama, Hidetoshi Ring-Expansion Reaction of Oximes with Aluminum Reductants |
title | Ring-Expansion Reaction of Oximes with Aluminum Reductants |
title_full | Ring-Expansion Reaction of Oximes with Aluminum Reductants |
title_fullStr | Ring-Expansion Reaction of Oximes with Aluminum Reductants |
title_full_unstemmed | Ring-Expansion Reaction of Oximes with Aluminum Reductants |
title_short | Ring-Expansion Reaction of Oximes with Aluminum Reductants |
title_sort | ring-expansion reaction of oximes with aluminum reductants |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268446/ https://www.ncbi.nlm.nih.gov/pubmed/22699568 http://dx.doi.org/10.3390/molecules17067348 |
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